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Gretchen Rubin

This week’s guest on Famous Failures is Gretchen Rubin.

Gretchen Rubin started her career in law—even clerking for Supreme Court Justice Sandra Day O’Connor—before stopping everything to become a writer. Though the transition was pitted with failure, it turned out to be one of the best decisions she made. Not only has she written three New York Times Bestsellers—Better Than Before, The Happiness Project, and Happier at Home—she’s also built an enormous readership, sold more than three million books, and started a weekly podcast called Happier with Gretchen Rubin. Her newest book, The Four Tendencies, will be published on September 12, 2017, and is currently available for pre-order.

Gretchen has sat for dinner with Daniel Kahneman, walked arm-in-arm with the Dalai Lama, been interviewed by Oprah, and now joins me, Ozan Varol, on an episode of Famous Failures. What follows is an edited version of our conversation. I hope you enjoy it as much as I did.

Looking back on your life, what has been the most valuable failure?

By far my most valuable failure was the publication of my biography of JFK called 40 Ways to Look at JFK.

As they say in the publishing industry, it did not find its audience.

That was an important moment for me because I felt very helpless, and frustrated. I poured all this time and energy into writing what I thought was a really, really great book, and I couldn’t do anything to help it sell.

And that’s when I became very interested in the idea of connecting directly with an audience. Fortunately for me this was just at the time that blogging was becoming easy enough that even somebody who was not technical could figure out how to do it. That got me thinking about how that might be a way that I could try to connect with an audience myself, apart from any gatekeepers like booksellers or book reviewers or television bookers or radio bookers.

What other failures have you found to be valuable?

I didn’t have success right away, and I think that was incredibly valuable.

A lot of creative people in a lot of different creative industries who experience early success start to think, “Well, this is the kind of person I am. I’m a hugely successful screenwriter. I’m a hugely successful TV writer. I’m a hugely successful advertising executive. I’m a hugely successful non-fiction writer. This is just my natural level.”

But the truth is—that’s pretty rare. Most successful creatives scrape by, fighting for every reader they have. They take nothing for granted. Early success is misleading, and if you’re not grounded, it can set you up for disappointment and failure long-term.

Success can boost egos, so when you do achieve that momentous success early on in your career then you think you’re essentially invincible.

I think you’re right. If you have a success right away you think, “Oh, I’m right. Everybody else should trust my judgment because clearly I’m brilliant.” Whereas in fact most people could use other people’s input.

You clerked for Justice O’Connor on the Supreme Court. How did you transition from that into writing?

When I was clerking, I had this moment, this epiphany where I realized I would rather fail as a writer than succeed as a lawyer—that’s when I knew it was time to take the risk. I remember thinking, “I might not have the guts to do this if I wait. I’ve got an idea. I want to do it. This is the time. What more am I waiting for to signal to me that this is the time to take the risk?”

So, that’s what I did.

Did you hit any roadblocks or struggles in entering the publishing world?

I applied to several agents before I found one willing to take me on—she was very young, a “Baby Agent” is the term she uses now, and just starting out like me.

At the time I thought, “I don’t know… she hasn’t been around that long. She doesn’t have that deep a client list.” I would’ve liked to have had a big, famous agent with a really well-known name. I definitely applied to some of those people and got turned down by all of them…Maybe I would’ve been better off if I had some fancy, famous agent?

But the fact is, my agent is absolutely brilliant. She’s extremely successful and even founded her own literary agency. And we’re perfectly suited for each other. She completely understands what I’m trying to do, and has really pushed me all along the way to try new things—some of which have been total failures that we’ve both learned from.

So, I guess the roadblock or struggle is that I just wasn’t sure about anything—from my agent to my writing—but it all worked out.

Are there any particular resources that you found helpful that you would recommend to others interested in becoming published authors?

I did a blog post called: A Question That I’m Often Asked: How Do I Become a Published Author?

In the blog post, I talk about the big lessons I’ve learned along the way, and I also list several extensive resources from Jane Friedman.

How do you fail when it comes to writing?

Before answering, let me just say there’s no one “right” way to write.

If you read a book that’s like, “The best way to do it is this,” the first thing you should think is, “Mmm, maybe not.”

I know many successful writers who do their “thing” in very different ways.

Having said that, I fail by letting my initial writing be bad—really bad. I take thousands of pages of notes, and then I just try putting those notes into my own words. I just sort of choke it out and edit it from there.

I feel tremendous relief once I have a beginning, a middle, and an end. Once everything is there on the page, I can go through and polish. I love to edit, but it’s hard to do original thinking when I’m editing, so I have to allow myself to write very badly and really push myself to take a stab at it.

What’s one piece of writing advice you would give to aspiring writers?

The one piece of writing advice that I feel qualified to give, and it works like a charm, is this: if you’re struggling to write something, like let’s say you’re struggling to write a law paper, the problem is you don’t have anything to say. Once you have something to say, it’s much easier to write.

Trying to write a 10-page paper about something you have no view about is not going to be easy. It’s just going to be terrible, because it’s going to be a bunch of words. I’m sure you’ve read papers like that where you’re like, “You have the same nonsensical statement that you’re just paraphrasing.”

That’s a really important point. I do see this a lot in law student papers. I always ask my students to step back and think along the way that you described: What is this sentence for? What is this paragraph for?

I completely agree.

What’s one thing you you’d like to leave the Famous Failures audience with?

This was a mantra that has really helped me: “Enjoy the fun of failure.”

I think people sometimes have this feeling of shame when they fail. Like, they want to pretend it didn’t happen. So, enjoying the fun of failure is trying to recast failure in a more lighthearted way.

Don’t try to ignore or re-categorize the failure—own it and have fun with it.

Failure is part of success—if you’re not failing, you’re not trying hard enough…not pushing the boundaries far enough.

If I’m just doing everything the way I’ve always done it, and everything’s just kind of trickling along, that’s not a good sign.

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